(R)-2-Chloro-1-(3-chlorophenyl)ethanol

Base Information

• Chemical Name: (R)-2-Chloro-1-(3-chlorophenyl)ethanol
• CAS No.: 142763-10-8
• Molecular Formula: C₈H₈Cl₂O
• Molecular Weight: 191.057
• DSSTox Substance ID: DTXSID50438879
• Nikkaji Number: J1.595.333K
• Wikidata: Q72456639
• Mol file: 142763-10-8.mol

Synonyms:(R)-2-Chloro-1-(3-chlorophenyl)ethanol;142763-10-8;(R)-1-(3-Chlorophenyl)-2-chloroethanol;(1R)-2-chloro-1-(3-chlorophenyl)ethanol;(R)-2-chloro-1-(3-chlorophenyl)ethan-1-ol;SCHEMBL98267;DTXSID50438879;LBSKQOSGSUKVDG-QMMMGPOBSA-N;AKOS006287644;(R)-2-chloro-1-(m-chlorophenyl)ethanol;AC-25513;AS-63847;(R)-2-chloro-1-(3'-chlorophenyl)ethanol;CS-0334136;(1R)-2-chloro-1-(3-chlorophenyl)ethan-1-ol;(R)-2-chloro-1-(3-chlorophenyl)ethane-1-ol;C72678

Chemical Property of (R)-2-Chloro-1-(3-chlorophenyl)ethanol

Chemical Property:

• Vapor Pressure: 0.00138mmHg at 25°C
• Melting Point: 110-120 °C
• Boiling Point: 285 ºC
• PKA: 12.94±0.20(Predicted)
• Flash Point: 119 ºC
• PSA: 20.23000
• Density: 1.328
• LogP: 2.61220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 189.9952203
• Heavy Atom Count: 11
• Complexity: 119

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-2-chloro-1-(3-chlorophenyl)ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Cl)C(CCl)O
• Isomeric SMILES: C1=CC(=CC(=C1)Cl)[C@H](CCl)O
• Uses: (R)-2-chloro-1-(3-chlorophenyl)ethanol is used in the preparation of benzimidazolyl pyridinones as IGF kinase inhibitors.

Technology Process of (R)-2-Chloro-1-(3-chlorophenyl)ethanol

There total 8 articles about (R)-2-Chloro-1-(3-chlorophenyl)ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

3-chlorophenacyl chloride (21886-56-6) → (S)-2-chloro-1-(3-chlorophenyl)-ethanol (174699-78-6) + (R)-1-(3-chlorophenyl)-2-chloro-1-hydroxyethane (106262-93-5,142763-10-8)

Guidance literature:

With D-glucose; nicotinamide adenine dinucleotide phosphate; In dimethyl sulfoxide; at 40 ℃;

DOI:10.1016/j.procbio.2019.09.037

Reference yield: 99.0%

3-chlorophenacyl chloride (21886-56-6) → (R)-1-(3-chlorophenyl)-2-chloro-1-hydroxyethane (106262-93-5,142763-10-8)

Guidance literature:

With D-glucose; D-glucose dehydrogenase; NADPH; potassium phosphate buffer; recombinant ketoreductase; In water; at 20 ℃; pH=7.0;

DOI:10.1016/j.tetasy.2005.08.037

Reference yield: 48.0%

vinyl acetate (108-05-4,9003-20-7) + (+)-2-chloro-1-(3-chlorophenyl)ethanol (106262-93-5) → (R)-1-(3-chlorophenyl)-2-chloro-1-hydroxyethane (106262-93-5,142763-10-8)

Guidance literature:

With Lipozyme TL IM; In tert-butyl methyl ether; at 40 ℃; for 12h; optical yield given as %ee; Enzymatic reaction;

DOI:10.1016/j.cclet.2012.01.008

upstream raw materials:

3-chlorophenacyl chloride

(+)-2-chloro-1-(3-chlorophenyl)ethanol

3'-Chloroacetophenone

3-chlorostyrene oxide

Downstream raw materials:

(R)-1-(3-chlorophenyl)-1-hydroxy-2-iodoethane

CL 316243

5-{(R)-2-[(R)-5-(3-Chloro-phenyl)-2-oxo-oxazolidin-3-yl]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

[R-(R*,R*)]-5-(3-chlorophenyl)-3-[2-(3,4-dimethoxylphenyl)-1-methyl-ethyl]-oxazolidin-2-one

Refernces

• 1、 Hu, Die,Wen, Zheng,Li, Chuang,Hu, Bochun,Zhang, Ting,Li, Jianfang,Wu, Minchen. "Characterization of a robust glucose 1-dehydrogenase, SyGDH, and its application in NADPH regeneration for the asymmetric reduction of haloketone by a carbonyl reductase in organic solvent/buffer system". . p. 55 - 62. Retrieved 2019/11/26.
• 2、 Xia, Shi Wen,Lin, Hui,Chen, Yong Zheng. "Preparation of (R)-2-chloro-1-(m-chlorophenyl)ethanol by Lipozyme TL IM-catalyzed second resolution". . p. 289 - 292. Retrieved 2012/05/05.